Gender: Male Age: 45 Location: N/A
|Introduction: Teen loses his virginity to sweet college girl|
By Wojo Martin
This is a re-working of a story I wrote a few years back. It’s a fairly straightforward stand-alone story about a recent high school graduate’s first sexual experience. He finds romance with a slightly chubby girl a few years older than himself. Most of my stories are about people dealing with pain, anger or guilt. This one is simply about two sweet young geeks finding summer love.
The story features consensual teen sex, with a male virgin. There is also oral sex and light cumplay.
Simon's life was anything but simple. He was like any other kid in high school, in love with the handful of beautiful, popular girls—girls that frankly had better options. He and his buddies wound up hanging out with each other every Saturday night. That would have been simple, he guessed, except for the fact that he was a romantic soul. He wanted to have a sweetheart. He wanted to make love to a girl. But, the girls he lusted after weren’t interested in him, and his buddies would have ragged on him if he went out with anything less than a gorgeous cheerleader type.
He was just as bad as any of them. Maybe worse than most. One night he ended up watching some old movie called "Say Anything." He remembered the scene where Lloyd’s female friend told him, “Don’t be a guy; the world’s full of guys. Be a man.” And when the local losers sat in front of the Gas-and-Sip and gave bad relationship advice to Lloyd. Simon didn't see himself in the romantic lead. He saw himself as the guy claiming that the boys hung out there without a single girl in sight "by conscious choice."
Walking home alone from the strip mall parking lot one night not long after, he came to his own “conscious choice.” In a week he was going to graduate from high school—Class of 2003. Nearly a decade later, as he was getting dressed for his wedding to a little nerd girl he loved with all his heart, he would look back on this night and declare it the turning point of his life.
It was time, by the gods, to stop playing high school games, he decided. No more longing in vain for prom queens and cheerleaders, no more wondering what his buddies would think if he went after a girl with less obvious physical allure. He wasn't lowering his standards. He was going to find a girl that made him laugh, that made him think, that made him feel something more than physical lust and a vague hope of an improved social status. He was going to make it simple. There had always been a little voice in his head that told him to stop trying to find a girl who looked like a wet dream and instead focus on finding a girl who made him feel happy and comfortable. He was finally going to listen to that voice.
About a week after graduation, he started a summer job at a kiddie amusement park: the kind with low-flying rides that entertained three-year-olds but left anyone over the age of seven less than impressed. It was work, and he liked being outside a lot better than he had liked working in the kitchen at a restaurant. Of course he had known his way around the kitchen, and he had to start out as a total novice at “KidzRock! Where we say, ‘Kids Rock!’”
He had to get trained by employees who had worked there in previous years. He found himself mainly in the company of bored high schoolers who looked down on him slightly for being older than them but knowing less about the job. On about his fourth day, he was sent to work on the airplane ride, and found himself in the company of someone entirely different. She was happy and friendly, interacting with the kids and treating Simon like a peer. This last part was especially nice for Simon, since she was a college girl two weeks shy of her twentieth birthday.
Her name was Cassandra. She was a short busty redhead with big blue eyes. With her freckled face and slightly chubby bottom, he might have missed her beauty three weeks ago, but with his new attitude, he realized that this girl was a really cool person. He had to lean over her while she worked the controls, and he couldn’t help but catching a whiff of her bright red hair. Man, he loved the scent of it. As a matter of fact, he snuck a few extra whiffs just to take the memory of her home with him. He innocently brushed against her a few times as they worked and once turned around and accidentally caught her in the boob with his elbow. He immediately apologized, but she was laughing so hard at his consternation over such an innocent matter that he suddenly felt very young. She went right on being chatty and comfortable with him, and he soon put it behind him. It was his best day at KidzRock by far.
The park was staffed by a mix of high school and college kids, but his status as a recent graduate, eighteen wonderful years old, provided him a chance to slide in with the older kids at the lunch table. And the joy of that was that these kids partied pretty hard and pretty often. He found himself allowed to tag along with a new crowd. By the end of the first week, he felt about three years older than he had at the beginning.
The first Saturday night found him invited to a house party packed with college kids on summer break. A month ago he would have found himself trying to make time with, and consequently being rejected by, slightly older versions of the girls that had rebuffed him in high school. But this was not the case anymore. Simon scanned the room for girls not standing in the big circle around the cluster of well-muscled jocks hammering back beer-bongs. He found a trio of girls sitting in a corner, drinking slowly and talking amongst themselves. He recognized one of them as Cassandra. He had an "in." He moseyed on over.
"Cassandra, hi! I just wanted to thank you for being patient with me the other day at work. You were really cool."
"Sure, Simon. Not a problem."
"Well, I'll let you get back to your friends. Looks like you were having a good time."
"Cass, who's your friend?" a short girl with glasses asked.
"Becca, this is Simon—um it starts with a W..."
"Well, Simon Walters, have a seat," Glasses ordered, making the third girl, who sported several facial piercings, slide over.
"Look out, Simon," Cassandra whispered as he shrugged and moved to let him sit down.
"Did she tell you to be careful?" Glasses said as he plopped down beside her. He didn't want to give Cassandra up, so he looked as if he had no idea what she was talking about. "I know she did. She tells me I'm a ballbuster."
"Really?" he said, mockingly covering his groin with his beer.
"So, Simple Simon, you're a typical young man, why you over here by us instead of by that gaggle of peroxides over there?" She slid her glasses down her nose and looked over the top of them at the beer-bong crowd.
"I came to say thank you to Cassandra."
"Could have done that at work."
"Becca, the kid was just being nice," the girl with nose, ear and brow piercings added, seemingly bored with the proceedings. "I'm sure he has other places he'd rather be. Let him go about his business."
"Is that what you want, Simple Simon? To leave us and go about your business? Or are you checking us out?"
"Wow, Cassandra!" he said. "I've met two of your friends, and I like almost half of them. Sorry to have interrupted." He got up to go.
"Hey, come back when you can stay longer," Glasses called out as he began to walk away. So much for the simple life and meeting a different group of girls.
He ran into Tony, one of the friendlier guys from work. He talked to him for all of about thirty seconds before Tony's girlfriend grabbed him by the hand and led him off. Simon turned to look around the room and found himself face to face with Cassandra.
"Sorry about Becca and Carmen. They are kind of snots to younger guys."
"Hey, I'm not upset with you, Cassandra. You've been nothing but wonderful to me. I hope I didn't get you into hot water with your friends."
"Fuck them. I don't base who my new friends are on whether or not my old friends like them. I decided that a couple years ago."
"H-mmm," he grunted, half-smiling. Cassandra looked at him questioningly. "I just decided that a couple weeks ago."
"And that's why you chatted us up instead of the peroxides?"
"Would you be grievously offended if I said yes?"
"Considering I just said pretty much the same thing to you, I think that would be a little unfair. Well, just remember that my friends have been around the block a few more times than you, and they saw right through that. They get pretty jaded. Some guys at school act like we should be grateful just that they are talking to us instead of the party girls."
"Well, I'm not trying to be condescending or anything. Geez, don’t you have to be in a lofty position to look down on others? I’m not really qualified for that.”
Cassandra looked less amused with this. “You don’t like yourself?”
“No, I kind of think I’m a neat guy. I just wish all this meeting people stuff was less complicated. Look, let me be straightforward. This might be blunt, be prepared for a shock!” he said with mock portent.
She picked up on his vibe and put a hand on his elbow as if lending him courage. “I’m ready, Simon.”
“Cassandra, I am hereby openly declaring that I find you interesting as a person and it would be pleasing to me if we had—normal—social—interaction."
"I also find that… acceptable."
"Sounds like Vulcan pillow talk," he said, raising an eyebrow like Spock.
"Dropping Star Trek references this early in the conversation? You really are comfortable with me."
"Well it seemed less geeky than the 'Iliad' shout-out I had kicking around in the back of my mind."
"Cassandra giving you a warning and you ignoring it?"
"Pretty much. Glasses tore me a new one and Piercings just wanted me to go away. And I hadn't even asked her if she had any more interesting places pierced!" Cassandra laughed. Wow! He liked her! And truth be told, she was physically attractive when you actually looked at her. Which he did. He took in her nice bust, pretty blue eyes and bright red hair you can't get from a bottle. Most of the girls he had known in school probably would have been a little put off by the fact that he fell silent and just stared like that. He had simply lost track for a moment.
"Simon, you are not exactly good at being subtle, are you?"
"Well, you're taking a good long look and I can see the wheels turning in your little head. Plus which, I don't know if you remember, but when I got close to you on the controls of the airplane ride, you smelt my hair."
"I remember. Your hair smells great. It's got more than one scent to it, too. One of those mixed scents that guys can't identify, but it's very... invigorating." She smiled again.
Much of the rest of the night was a blur. They didn't drink that much, but got together in a corner and talked on and on for hours. Sometimes they talked about work or people, but often about "Firefly" or "Lord of the Rings." She had a moist spot for science fiction that rivaled his hard-on for swords and sorcery. At some point, he had been looking at the curve of her breasts against her "Joss Whedon is My Master Now" t-shirt for just a little too long to tolerate, and he leaned in and kissed her. It was a nice soft kiss with just a touch of dancing tongues. The scent of her beautiful red hair filled his nostrils. He could have stayed in the moment forever—if it weren't for the feeling of someone watching them. He gently pulled back. Glasses was standing over them looking in askance.
"Cass, I know you're probably having fun re-living the prom, but Carmen and I are bored to tears with this place. You riding home with us?"
"Well, Becca, I believe I'll find my own way home, since I am obviously having making out with this handsome young man here."
"Um-Cassandra—I rode my bicycle here. I only live a mile away."
Glasses guffawed. It wasn't appealing.
"Well, Becca, WE have decided to accept your ride back to my house," Cassandra said.
"It's really kind of you, to offer," Simon said with a shit-eating grin.
The ride to Cassandra's was really rather quiet. Glasses and Piercings were not amused with Simon’s presence. And Cassandra and Simon were fairly busy sucking face in the backseat. He did make sure to thank Glasses again for the ride as he unloaded his bicycle from the trunk of her car.
Cassandra stayed with her parents during the summer, but it was a huge suburban house and she had her own entrance—kind of like Fonzie's pad at the Cunningham's house. Her room looked a lot different, though. A big king size bed with plenty of plenty of girly covers and walls decorated with posters of David Boreanaz, Nathan Fillion and Adam Baldwin. She was a hardcore Browncoat, but he noticed that when she walked into the room she paused for a moment, kissed her fingertips and touched her autographed picture of Anthony Stewart Head.
"Cassandra, I'm looking forward to this more than you can imagine, but if James Marsters or Nicolas Brendon turns up in the bed, I'm leaving."
"Little boy, if James Marsters or Nic Brendon turns up in my bed, I'll pay you 1000 bucks just to get it all on video!" Man, he really liked this chick. And even considering his serious naiveté, Simon was certain he was going to have his first ever sexual experience; with her; right now.
He went right for her breasts as soon as they began to kiss, and she was more than okay with that. He was amazed by how many different qualities her breasts had. They were warm and felt full in in his hands. They moved easily, but were also firm enough that they always returned to their perfect position. He cupped them fully for a while, and then, heart pounding a little faster, he pinched the nipples gently. Even through her shirt and bra, he could feel them harden in response. She pulled off both of their shirts after about ten seconds of that.
She led him to the bed and laid him down. She straddled him and began to trace designs on his chest. “No point in tracing runes,” he said softly. “I’m already under your spell.”
“You are such a sweet guy, Simon.” She kissed him again. “I enjoyed talking to you all night tonight. I’m really glad we’re doing this.” She looked down at him and noticed that while he was actually listening to her, he was quite enthralled by her full breasts. She touched him on the end of the nose, bent down and kissed him again and then sat upright to give him a nice view.
She ground against the front of his shorts, and smiled as he reached his hips toward her. She took her own bra off, letting the objects of his fascination tumble out before him. "Damn!" he whispered.
"Simon. I have a question for you. Am I—um—popping your cherry tonight?"
"Yes, and I have never met anyone who I’ve wanted to have be my first like I want you to be, Cassandra. You are so incredibly sweet and beautiful."
"Oh, sweet baby boy, I'm gonna treat you good. Just relax and enjoy, because I got a long list of things I think you're gonna like."
"That sounds good," he said, massaging her breasts and wondering what could feel better than her grinding against the front of his shorts had just felt. Cassandra soon removed those shorts. She slid down, kissing his chest, and finally settling her full lips on his erection. He bucked and raised his hips high off the bed.
“Easy, sweetie. Let Cassandra do the work.” He relaxed the best he could and let her find her rhythm. She was no pro, but she had done this before, and all Simon knew was that it was incredible. He had imagined what it would be like to have a girl that he really liked giving him his first blowjob, but he hadn’t imagined how natural it would feel. He felt safe with Cassandra, and her touches brought him nothing but pleasure. She would tease the underside with little licks and twirls of the tongue, and then take him fully into her warm, soft mouth. He had thought it would be all sucking and pulling, but it was playing and teasing and kissing and teasing as well.
After a few minutes, he could tell that he was about to cum, and wondered exactly what he should do about that. “Cassandra,” he groaned, “I’m gonna…”
"Let it go, sweet baby," she whispered. He did, and she aimed it at her breasts. "Pearl necklace," she whispered with a little laugh. “God, I love that.” Simon realized he did, too. She lowered herself onto him, crushing her breasts against him and sliding a little to spread his semen between them. It certainly was not what he was expecting, but he liked it. In the fog of his lust-saturated mind, it seemed fair somehow. “I’m not into really freaky stuff,” she whispered with a grin, “but I do have my little kinks.”
“Cassandra, can I see… can I kiss yours, too?”
“I’d like that, Simon.” She rolled off him for a moment as she slid out of her own shorts and panties and kicked them to the floor. She lay naked beside him, and kissed him for a little bit, offering her neck so that he could start moving downward. He slid down her neck, kissing her frequently. He kissed the base of her breasts, and built the courage to work to her nipples. When she moaned softly, he began to suck them and play at them with his tongue. His work may have lacked polish, but it was sweet and obviously pleasing to Cassandra. She had some experience, having completed two years of college, but she was in no way jaded. A sweet boy gently kissing and kneading her breasts moved her both physically and emotionally.
With desire, and just the tiniest touch of fear, Simon kissed his way across her stomach and down to her fragrant nethers. Here, he was even less certain of what to do. He had read stories and even watched and (re-watched) videos, but none of them prepared him for the tenderness he felt for Cassandra. Nor did they prepare him for the wonderful combination of sensations that greeted him. He loved the way she smelled, and when he began to kiss her labia and gently flick at them with his tongue, he found that the taste was strong but wonderful. Wine had been strong the first time he tasted it, but he had loved it from the start. He felt the same way about Cassandra’s sex.
Boldly, for him, he brought one of his long thin fingers up to her slick opening and slowly slid it up inside of her. It was so warm and soft. He could tell by its texture that the inside of her was very sensitive. He gently probed her and moved his kisses higher up on her labia. He knew what a clitoris was, and he sought for it with his lips. He found it and began to kiss it tenderly. Cassandra groaned slightly, and he feared he may have touched her in a place that was too sensitive. To his surprise, she reached down and gently but firmly pushed his face down a little harder. He began to use his tongue more freely, and this time recognized her groans as expressions of pleasure.
He felt… sexy and desirable. He had felt that way from the first moment she had returned his impulsive kiss, and felt even more so when she had chosen to pleasure him with her mouth. Now, he felt like he had become something more than he was a few minutes ago. He was a man that could please a woman!
Her moans stopped rather abruptly and were replaced by a series of sharp breaths and a quivering all through her body. Then, she relaxed and seemed very calm. He knew that he had given her an orgasm. It didn’t involve the screaming and thrashing he had expected, and he was glad of it. He would someday love to try wild sex, but this had been tender and sometimes playful lovemaking. He was finding it very fulfilling.
He kissed his way back up to her lips, and she kissed him passionately and then gently stroked his hair. He returned the favor, but also pulled a lock of her hair to his face and inhaled deeply. “Everything about you feels, tastes and smells so incredible,” he whispered.
“Wow!” she said softly. “Was I ever right about you. You’re a kind and gentle man. Would you like to make love now?” Simon closes his eyes, took a deep breath and nodded slowly but definitively. Cassandra reached into the bedside drawer and pulled out some condoms. She opened one up and slid it over his penis, which had returned to a full erection. Youth has its advantages. "Are you ready, Simon?" she said softly. He nodded. "You are a beautiful man, and I am glad to share this moment with you."
She straddled his erection and gently guided it into her. Suddenly he knew what it was that would feel so much better than her grinding against him with their clothes on. She rocked back and forth gently for a while, changing angles and positions and letting him feel the pleasure of being inside her. He reached for her breasts, and she nodded as he began to massage them. She slowly pulled herself to an upright position and he reached up, trying to follow her breasts. She pushed him back down and began to play with her own breasts as she gently rode him. Soon, she dropped a hand to her sex and began to massage her clit as she rocked back and forth. He watched in amazement as she began to slowly heat up. Her creamy skin turned pink beneath her freckles.
Seized with an overwhelming outpouring of energy and lust, he reached up to her full hips and grabbed them firmly. He began thrusting up into her with all of his might. She was a little surprised, but adjusted quickly to this thrilling new stimulation. "Oh, hell yes," she whispered as he continued to pick up speed. She closed her eyes and began to nod emphatically. "You've got the spot. Go with it now!" He drove himself in as deeply as he could go, time after time. She began to emit an occasional little squeak and then a few loud moans. Simon didn't know much, but he knew that she was about to cum. She unleashed her passion with a triumphant, "Oh yes! Oh yes! Oh yes!" and then collapse gently on top of him.
While she was older than Simon, she wasn't older by much, and even a good hard second orgasm didn't leave her spent. Simon lay motionless and a little uncertain, but she knew what he needed. "Roll me over and take me until you finish, Baby."
Simon now knew what he should do. He put Cassandra on her back, and she drew her heels almost all the way up to her plump little rump while letting her knees fall to the sides a bit. He crawled in between her legs and drove himself firmly into her welcoming body. He grabbed her by her surprisingly firm haunches and launched himself wildly for a moment until he found that there were different angles and speeds he could try. He decided to try and make it last. At one point, he picked her bottom up off the bed and let her grind her sweetness against him. He brought himself to a kneeling position and drove himself into her and pressed his groin against the ginger hair of her womanhood while he reached down and tweaked her nipples. "By the gods, I love your tits," he whispered. She smiled and reached down between her legs and diddled herself while he enjoyed them for a few moments longer. Then he set to work on finishing their lusty enterprise. He realized that he had found an angle that hit the spot she had been touching on her own. Her pleasure inspired him, and he drove himself in on that angle for as long as he could. He finally let go, and was certain there was no way the condom could hold so much semen, but when he collapsed and rolled away, everything seemed intact.
They both breathed heavily for a few moments. She handed him a Kleenex, and after a moment of looking perplexed, he figured out exactly how to remove the condom without making a mess.
Freed for a moment from his passionate intoxication, he found his humor. "Well," he said casually. "I'll call ya." He got up and pretended he was about to leave. She didn't buy it for an instant. She just smiled and patted the bed next to her. He grabbed his cell phone from his pants and sat down next to her on the bed. She draped her arms over his shoulders from behind and kissed his shoulders as he began to text. "Mom, not coming home 2nite. Staying w friend. Safe n sound." He felt her breasts against his bare back. "n happy!" he added.
As he fell asleep with her arm across his chest that night, he dreamt that he stood outside her window at dawn with a boom-box. A classic Peter Gabriel song filled the air, and Simon didn’t feel like just a guy. He felt like a man.
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